Anthracene dyes and making the same.



To all whom it may concern:

UNITED STATES PATENT OFFICE.

HUGO WOLFE, OF LUDWIGSHAFEN-ON-THE-BHINE, ASSIGNOR TO BADISOHE ANILIN & SODA FABRIK, OF LUDWIGSHAFEN-ON-THERHINE, GERMANY, A CORPO BATION.

1,063,000. No Drawing.

Be it known that I, Huoo WOLFF, Ph. D., chemist, subject of the Grand Duke of Baden, residing at Ludwigshafen-on-the-. Rhine, Germany, have invented new and useful Improvements in Anthracene Dyes and Making the Same, of which the follow ing is a specification.

, The specifications of Letters Patent Nos. 809,892, 818,992 and 818,336 describe the production of coloring matters by treating, with caustic alkali, a compound containing a benzanthrone group. Members of this class of coloring matters contain the dibenza-nthrone grouping, and in the specification of Letters Patent N o. 7 96,393 it is stated that such coloring matters can be further treated with a nit-rating agentand that the products of nitration can, if desired, 7 be reduced. Suchnitration products and their reduction compounds constitute from olive-green .to blue-green coloring matters. 3

The specification of Patent No. 906,367

a A (cf. British Patent No. 20,837/06) describes the production of coloring matters by first halogenating a compound co-nta mng a henzanthrone group and then acting on such halogenating benzanthrone derivative with caustic alkali; such coloring matte-rs differ from the coloring matters described in the specification of Patent No. 818,336 in that they contain the iso-dibenzanthrone groupmg:

They are included under the term isodibenzanthrone bodies. I have now found that these iso-dibenaanthrone compounds can be treated with a nitratingagent and i that the nitration products can, if desired,

be subjected to reduction and that, in each case, valuable coloring matters can be obtainedwhich dye vegetable fiber very fast shades which are generally of a bluer tinge ANTHBACENE DYES MAKING THE SAME.

'dibenzanthrone boiling nitrobenzene.

- blue. In this example,

"fifty. it; into water and work up in the boiling nitrobenzerie.

Patented May 27, 1913.

than those produced by the products obtain able according to the specification of Letters Patent No.7796,393. The following are examples of how my invention can be carried into practical effect, but the invention is not confined to theseexamples. The parts are by weight.

Example 1: Suspend ten parts of iso- (obtainable according to Example 9 of the specification of British Letters Patent N o. 20,837/06) in one hundred parts of nitrobenzene, and add twenty, parts of eighty per cent. nitric acid. Warm the mixture gradually to from fifty to sixty degrees centigrade and maintain this temperature until, from a test port-ion, it is seen that no unaltered iso-dibenzanthrone is present. When the mixture is cold, filter ofl the product, wash it with nitrobenzene and alcohol, and dry it.

The coloring matter so obtained 1s,

when dry,

sulfuric acid and a violet-blue solution in Ityields a blue vat in alkaline hydrosulfite and from this vat veges table fiber is colored blue shades which, upon washing and drying, become a very fast the nitrobenzene can be replaced by other indifferent solvent, or diluent, for example glacial acetic acid.

Example 2: Dissolve ten parts of isodibenzanthrone ,in one hundred parts of ninety-seven per cent. sulfuric acid and add thirty-two parts of ten per cent. nitric acid. Heat the mixture for about six hours at from to sixty degrees centigrade, then pour usual manner. The coloring matter obtained appears to be identical with thatdesciibed in the foregoing example. I Example'3: Suspend ten parts of the product obtainable according to the foregoing Example 1 in five hundred parts of a ten per cent. solution of sodium sulfid and boil the whole for about thirty minutes. When the mixture is cold, filter off the reduction product and wash and dry it. It is, when dry, a powder with a metallic'luster and yields a green solution in concentrated sulfuric acid and a greenish blue solution in With alkaline hydrovat which dyes vegesulflte it yields a blue those produced table fiber shades similar to by the nitro product.

My new coloring matters are characterized a dark blue powder i which yields a green solution in concentrated by being dark powders which ield green solutions in concentrated s ric acid, yiolet-blue to greenish blue solutions in boiling nitrobenzene, and yield blue vats with alkaline hydrosulfite from which vats cotton is dyed blue shades.

Now what I claim is 1. The process of producing new coloring matters of the anthracene series by treating v, containing nitrogen which coloring matters upon the application of and that the I the same may conform to the record of Signed and sealed It is hereby certified that in Letters Patent No. 1,063,000,

yield green solutions concentrated sul furic acid, violet-blue to gre'enish blue solum hand in the presence of two subscribing 35 witnesses. v

HUGO WOLFF.

Witnesses:

- J. Am. LmID,

A. 0. Tin-MANN.

granted May 27, 19135 Hugo Wolfi, of Ludwigshafen-on-the-Rhine, Germany for an improvement in Anthracene Dyes in the printed specification requiring correction as the group l and Making the Same, an error'appears follows: 1,. lines 3446, for

said Letters Patent should be read with this correction. therein that the case in the Patent Ofice. this 19th day of August,

moms nwme,

of Patent!- by being dark powders which ield green solutions in concentrated s ric acid, yiolet-blue to greenish blue solutions in boiling nitrobenzene, and yield blue vats with alkaline hydrosulfite from which vats cotton is dyed blue shades.

Now what I claim is 1. The process of producing new coloring matters of the anthracene series by treating v, containing nitrogen which coloring matters upon the application of and that the I the same may conform to the record of Signed and sealed It is hereby certified that in Letters Patent No. 1,063,000,

yield green solutions concentrated sul furic acid, violet-blue to gre'enish blue solum hand in the presence of two subscribing 35 witnesses. v

HUGO WOLFF.

Witnesses:

- J. Am. LmID,

A. 0. Tin-MANN.

granted May 27, 19135 Hugo Wolfi, of Ludwigshafen-on-the-Rhine, Germany for an improvement in Anthracene Dyes in the printed specification requiring correction as the group l and Making the Same, an error'appears follows: 1,. lines 3446, for

said Letters Patent should be read with this correction. therein that the case in the Patent Ofice. this 19th day of August,

moms nwme,

of Patent!- 

